The inside story of how Uber fought New York’s City Hall and won

As some Fast Company readers probably know, in August 2018, the New York City Council capped the total number of Uber and Lyft drivers allowed on the road. This was sweet revenge for New York City Mayor Bill de Blasio, who, three years earlier, suffered a humiliating defeat at the hands of Uber when he tried the very same thing. A lot has changed at Uber since 2015, most notably the replacement of founder and CEO Travis Kalanick with Dara Khosrowshahi, the former CEO of Expedia.

Khosrowshahi entered Uber at a time of turbulence and quickly set out to calm the waters. He did, settling a long-running dispute with Waymo, another with the City of London, and generally sought to avoid confrontation at all times and pretty much at all costs. That gave de Blasio an opening to try to impose caps again.

Unlike the 2015 fight, which is detailed below, Uber’s approach in 2018 didn’t work. The taxi cartel remained as vicious as they’ve always been. The recipients of their campaign largesse at City Hall and in the City Council were just as eager to do the bidding of their donors as they’ve always been. And the kind of bare-knuckled brawl Uber waged in 2015 was replaced by a kinder, gentler campaign that utterly failed.

Turns out, when it comes to breaking cartels, soft just doesn’t work. Khosrowshahi’s long-term ambition for Uber–a less turbulent reputation heading into a 2019 IPO–may make sense in the aggregate, but in every city across the world, it also leaves the company highly vulnerable to attacks from the entrenched interests, politicians, regulators, advocates, and competitors they’ve beaten…

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